Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate → Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394209ノート

反応式

HRID 394209 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[C:11]=1/[CH:12]=[CH:13]\[C:14]([NH:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[O:15])[C:5]([O:7][CH3:8])=[O:6]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[C:10]2[C:11]=1[CH:12]=[CH:13][C:14](=[O:15])[N:16]2[C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24]

参加物

3

反応物 1

HCID 69919937Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate

生成物 1

HCID 22648178Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Methyl 3,5-dibromo-4-{(1Z)-3-[(2,6-dichlorophenyl)amino]-3-oxoprop-1-enyl}benzoate (1.25 g)(contaminated with 20% of the E isomer) was dissolved in dimethylformamide(36 mL) and the solution degassed with argon. Copper (I) iodide (340 mg) and dry potassium carbonate (468 mg) were added and the mixture heated to 80° C. for 30 min. The reaction mixture was poured into 5% ammonium hydroxide solution and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with 80% hexane: 20% ethyl acetate to give the title compound.

後処理

  1. customthe solution degassed with argon
  2. additionCopper (I) iodide (340 mg) and dry potassium carbonate (468 mg) were added
  3. additionThe reaction mixture was poured into 5% ammonium hydroxide solution
  4. extractionextracted into ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 80% hexane

出典と根拠

ORDレコード
ord-50f029a29e7c40aa80bf4bac3d5fbc1b
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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